Holmes: Sandler as 'Jill' Will Break Your Heart

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While the thought of Adam Sandler dressed as a woman may not sound like tear-jerker material, Sandler's Jack and Jill co-star Katie Holmes insists that the funnyman brings some serious heart to the upcoming comedy romp.
"She's got a sweetness to her," explains Holmes of Sandler's character, Jill. "I feel like Adam did a great job of creating a character who is not only funny, but someone who kind of breaks your heart and you can also relate to."
The "sweet" side of Jill may have earned a soft spot in Katie, but she acknowledged it was even more impressive to watch his comedy chops in action, finding it difficult to film a scene together without breaking character. "I've been a fan of Adam's forever and he's so funny, obviously. I did laugh a lot; I'm not going to lie. I tried to hold it in."
Sandler delivered his dual sweetness and signature silliness to the film's Sunday premiere, telling Entertainment Tonight the reality of playing both characters was a pain and a pleasure. On the one hand, he complains the bra and heels that come with the territory of womanhood were torturous, but with it came the opportunity to play out a long-time fantasy.
"My wife is very comfortable with me playing a lady. We have talked about that many times in the sack, and we got to live it out," he jokes.
Jack and Jill drops into theaters this Friday, November 11.